Christopher Cross’s “Sailing” became his first US No. 1 single after following his debut hit “Ride Like the Wind” in 1980. Although its opening verse and chorus came to him quickly in a small apartment, Cross spent roughly two years completing the bridge, aiming to break out of the song’s modal structure with key changes.

Cross initially doubted that the introspective track could succeed as a single and thought Warner Bros executive Mo Ostin was mistaken to release it. Instead, “Sailing” became a major hit and won three Grammy Awards, including Song of the Year.